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Loss of thetert-butyloxycarbonyl (Boc) protecting group under basic conditions

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
35
Issue
30
Identifiers
DOI: 10.1016/s0040-4039(00)73512-x

Abstract

Abstract Reaction of 3, the N-Boc, O-tosyl derivative of phenylalaninol, with base leads to loss of the Boc and tosyl groups and formation of oxazolidinone 9. Similar reactions have also been examined. A mechanism to explain loss of the Boc group under basic reaction conditions is proposed.

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